CN106176716A - The new application of daphane diterpene compound pimelotide C - Google Patents
The new application of daphane diterpene compound pimelotide C Download PDFInfo
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- CN106176716A CN106176716A CN201610560758.XA CN201610560758A CN106176716A CN 106176716 A CN106176716 A CN 106176716A CN 201610560758 A CN201610560758 A CN 201610560758A CN 106176716 A CN106176716 A CN 106176716A
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- pimelotide
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- daphane
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/83—Thymelaeaceae (Mezereum family), e.g. leatherwood or false ohelo
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Abstract
The present invention provides the new application of daphane diterpene compound pimelotide C, i.e. daphane diterpene compound pimelotide C application in preparing anti-hepatitis B medicine.Also providing for the pharmaceutical composition of a kind of anti-hepatitis B virus, containing the daphane diterpene compound pimelotide C of 0.1 99%, remaining is pharmaceutically acceptable carrier and/or excipient.HBV inhibitory activity and cytotoxicity experiment are proved at HepG2.2.15 cell through compound pimelotide C: compound pimelotide C can effectively suppress the generation of HBsAg, IC50Being 0.016 μ g/mL, TI value is 355.63, is significantly higher than positive control lamivudine.
Description
Technical field
The present invention relates to daphane diterpene medicine, new particularly to daphane diterpene compound pimelotide C
Purposes, specifically daphane diterpene compound pimelotide C application in preparing anti-hepatitis B medicine.
Background technology
Showing according to the relevent statistics, the whole world about artificial chronic viral hepatitis B more than 300,000,000 virus (HBV) carrier, China accounts for
Half.Hepatitis B virus infection has become one of global principal disease affecting human health, owing to HBV infection can cause
Chronic hepatitis, liver cirrhosis and primary hepatocarcinoma, therefore become one of nine big diseases affecting human longevity.Due to Chronic HBV sense
Dye person occurs the Relative Risk of hepatocarcinoma to be 217 compared with noncarrier, and therefore in the whole world, annual about 2,000,000 people die from hepatitis B
The liver cirrhosis caused and hepatocarcinoma, and China is the district occurred frequently of hepatitis B, there are about 250,000 people every year and die from relevant to hepatitis B slow
Property hepatopathy (liver cirrhosis and hepatocarcinoma).Above-mentioned disease brings massive losses to people's health and national economy.Therefore, seek the lowest
The Anti-HBV drugs of poison has become instant problem.
Natural product is various due to structure complexity, has therefrom found the novel lead compound of high-efficiency low-toxicity, action target spot
Through becoming the important component part of novel Anti-HBV drugs research and development.According to statistics, it is proven to have by internal and external activity screening
The natural product type of potential Anti-HBV effect includes lignanoid, terpenoid, alkaloid, flavone, coumarin, cyclic peptide etc..Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis) is
The alabastrum of thymelaeceae Flos Wikstroemiae Dolichanthae platymiscium Wikstroemia chamaedaphne (Bge.) Meisn. (Wikstroemia chamaedaphne Meissn), spends little, yellow, number
Piece lining up the raw umbellate cyme in top, carry several panicle that assembles again, alabastrum powder is yellow green, and main product is new in Shanxi
Deep red.Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis) acrid in the mouth warm in nature, slightly poisonous, it to be used as medicine with Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis) in the province such as Shanxi, Gansu and cure mainly removing water retention by purgation, relieving constipation, for water
Swelling is full, and phlegm retention is gathered, cough with dyspnea dyspnea with fullness of the chest, schizophrenia, epilepsy etc..Clinical research shows, Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis) leaf water extract has bright
Aobvious sedation, Wikstroemia chamaedaphne (Bge.) Meisn. can make irritability patient quiet, and depressibility patient's emotion is enlivened, and worried sexually transmitted disease (STD) people has been alleviated.
In China's tradition medication, Wikstroemia chamaedaphne (Bge.) Meisn. uses as anti-early pregnancy drug can make progesterone level, Serum HCG water
Pancake is low, and effect and prostaglandin, mifepristone are suitable.
Daphane diterpene is primarily present in thymelaeceae and euphorbia plant, and previous research shows this compounds pair
HIV has certain inhibitory action [daphane diterpene ortho-ester compounds, its pharmaceutical composition and preparation side thereof with virus
Method and application, the patent No.: CN201110234308.9；1-alkylation daphane diterpene and preparing anti-hiv drug
In purposes, the patent No.: CN201410308774.0]；Additionally, this compounds also shows fine function of tumor inhibition [Flos Genkwa
In new daphane diterpene-kind compound and its production and use, the patent No.: CN200910010388.2].
At present the report about daphane diterpene pimelotide C (see structural formula I) only limits 2 documents, opens most
Originating this compound existing is that Australian scholar in 2010 is obtained from Isolated From Thymelaeaceae Species Pimelea elongata, and initially obtains
Must be the mixture of two compounds, its total recovery 0.34mg/100g, content be the lowest, and separable programming is complicated, does not also report
Any pharmacologically active (Daphnane-and Tigliane-Type diterpenoid esters and orthoesters
from Pimelea elongate,Journal of Natural Products,2010,73,1907-1913).Other one
Document be Shenyang Pharmaceutical University of China scholar be also that its yield is from Isolated From Thymelaeaceae Species Daphne genkwa isolated
2.4mg/100g, content is general, and separable programming is also extremely complex, they this compound is carried out tumor cell HeLa,
MCF-7, HepG2, HCT116, A549, A375-S2, HT1080, HL60, U937, K562 screening active ingredients, this compound shows
Certain suppression tumor promotion (Daphnane-type diterpenes with inhibitory activities
Against human cancer cell lines from Daphne genkwa, Bioorganic&Medicinal
Chemistry Letters, 2013,23,2,500 2504).
But so far, prior art is not lived about daphane diterpene compound pimelotide C resistance of hepatitis B
Property report, there is no the report of they and pharmaceutical composition thereof the application in the medicine of preparation or treatment hepatitis B yet
Road.
Summary of the invention
It is an object of the invention to provide the new application of daphane diterpene compound pimelotide C, i.e.
Pimelotide C application in preparing anti-hepatitis B medicine；Daphane diterpene pimelotide C medicine is provided
Compositions；The preparation method of daphane diterpene compound pimelotide C is provided.
To achieve these goals, the present invention provides following technical scheme:
Daphane diterpene compound pimelotide C application in preparing anti-hepatitis B medicine, described
The structural formula of daphane diterpene compound pimelotide C is:
The pharmaceutical composition of a kind of anti-hepatitis B virus, containing daphane diterpene compound pimelotide C.Also
Daphane diterpene compound pimelotide C itself directly can be used as the medicine of anti-hepatitis B virus.
The pharmaceutical composition of a kind of anti-hepatitis B virus, containing the daphane of 0.1-99%, preferably 0.5-90%
Diterpene compound pimelotide C, remaining is pharmaceutically acceptable load the most acceptable, nontoxic and inert to humans and animals
Body and/or excipient.
Described pharmaceutical carrier or excipient are one or more solids, semisolid and liquid diluent, filler and medicine
Tetramune adjuvant.The pharmaceutical composition of the present invention is used with the form of per weight dose.The medicine of the present invention can be through note
Penetrate (intravenous, intramuscular injection) and oral two kinds of forms are administered.
The preparation method of a kind of daphane diterpene compound pimelotide C that the present invention provides, takes Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis), uses
95% alcohol reflux twice, each 3 hours, merges ethanol extract, and recovered under reduced pressure is to without alcohol, with the steaming adding same volume
Distilled water is dissolved, and then extracts by ethyl acetate, and extract concentrate drying becomes extractum, and extractum dissolves with 80% ethanol and is adsorbed in
On silica gel, room temperature is placed and is volatilized solvent, grinds after sieving through silica gel column chromatography, by volume ratio 7:3, the petroleum ether-second of 5:5,3:7
Acetoacetic ester gradient elution, obtains 3 components A-C, and component C is suppressed standby in ODS C-18gel post, by volume ratio 5:95 extremely
The methanol-water gradient elution of 95:5, obtains 5 stream part C1～C5；C4 is through Sephadex gel filtration chromatography, with volume ratio 1:1 chlorine
Imitation-carbinol eluting, obtains 6 flow point C4-1～C4-6；Flow point C4-3 is prepared through HPLC, washes with volume ratio 75:25 acetonitrile-water
De-, purification obtains compound pimelotide C.
Compared with prior art beneficial effects of the present invention: through compound pimelotide C at HepG2.2.15 cell
HBV inhibitory activity and cytotoxicity experiment are proved: compound pimelotide C can effectively suppress the generation of HBsAg, IC50For
0.016 μ g/mL, TI value is 355.63, is significantly higher than positive control lamivudine.Daphane diterpene pimelotide C chemical combination
Thing can be in the application in preparing anti-hepatitis B medicine.
Detailed description of the invention
In order to be more fully understood that the essence of the present invention, the present invention will be further described by embodiment below, but not with
This embodiment limits the present invention.
Embodiment 1
Daphane diterpene compound pimelotide C is to HBsAg, HBeAg secretion and the medicine to HepG2.2.15 cell
Thing toxicity test.
The cytotoxic assay of compound pimelotide C:
HepG2.2.15 cell, through digestion, is prepared as 2 × 105The cell suspension of/mL, is inoculated in 96 holes with 100 μ L/ holes thin
In born of the same parents' culture plate, after 48 hours cultivate, add the variable concentrations sample liquid of doubling dilution, continue to cultivate and (within every 3 days, change liquid in 9 days
Once), detect cell survival rate with mtt assay, determine the impact of sample cell growth, calculate TC50, and determine cytoactive >=
The sample concentration of 90% is for detecting Anti-HBV effect further.
Mtt assay detecting step: cell, after experiment is cultivated, discards culture fluid in culture plate, adds in the culture hole of every hole
The MTT solution 5 μ L of new culture fluid 95 μ L and 5mg/mL, shakes up, and puts 37 DEG C and cultivates 3-4 hour, it is seen that has bluish violet to crystallize in hole
Formed, carefully suck the solution in plate, add DMSO 100 μ L/ hole, concussion, make crystallization fully dissolve, microplate reader measures
Absorbance value, mensuration wavelength is 490nm.
Compound pimelotide C suppresses the secreting active mensuration of HBsAg and HBeAg:
HepG2.2.15 cell, through digestion, is prepared as 2 × 105The cell suspension of/mL, is inoculated in 96 holes with 100 μ L/ holes thin
In born of the same parents' culture plate, after cultivating 48 hours, add the sample liquid (sample concentration during cytoactive >=90%) of series concentration, simultaneously
If being not added with the blank of sample, continuing to cultivate 9 days (changing liquid once in every 3 days), collecting supernatant, using Shanghai industry Ke Huasheng
HBsAg and the HBeAg ELISA diagnostic kit of thing technology company, is operated by test kit description, detection
HBsAg and HBeAg level in HepG2.2.15 cell conditioned medium, calculate sample to the suppression ratio of HBV antigen and to suppression ratio >=
The sample of 50% calculates IC50With therapeutic index (TI=TC50/IC50).Positive control is lamivudine (3TC).
As a result, experimental result is shown in Table 1
Table 1, compound pimelotide C at HepG2.2.15 cell to HBV inhibitory activity and cytotoxicity
Conclusion: compound pimelotide C can effectively suppress the generation of HBsAg, IC50Being 0.016 μ g/mL, TI value is
355.63, it is significantly higher than positive control lamivudine.
Embodiment 2
The preparation of compound pimelotide C and sign: take Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis) 500g, by 95% ethanol (5L*2) reflux, extract,
Twice, each 3 hours, merging ethanol extract, recovered under reduced pressure, to without alcohol, is dissolved with the distilled water (400mL) adding same volume,
Then carrying out extracting 3 times by ethyl acetate (1L), extract concentrate drying becomes extractum (100g), and extractum dissolves with 80% ethanol to be inhaled
Investing on silica gel, room temperature is placed and is volatilized solvent, grinds after sieving through silica gel column chromatography, with the petroleum ether-acetic acid of 7:3,5:5,3:7
Ethyl ester gradient elution, obtains 3 components A-C, and component C is suppressed standby in ODS C-18gel post, and the methanol of 5:95 to 95:5-
Water gradient elution, obtains 5 stream part C-1～C-5.C-4, through silicon Sephadex gel filtration chromatography, washes with chloroform-methanol (1:1)
De-, obtain 6 flow points；Flow point C-4-3 is prepared through HPLC, acetonitrile-water 75:25 eluting, and purification obtains compound pimelotide
C(35mg).The Structural Identification of this compound by with document [Hayes, P；Journal of Natural Products,
2010,73 (11), 1907-1913] carbon modal data contrast determined.
The spectral data of compound pimelotide C is:1H-NMR(600MHz,CDCl3),δH: 2.35 (1H, dd, J=
8.8,3.5Hz, H-1), 4.87 (1H, s, H-5), 3.55 (1H, s, H-7), 3.70 (1H, d, J=2.2Hz, H-8), 3.08 (1H,
D, J=8.0Hz, H-10), 2.48 (1H, m, H-11), 2.12 (1H, m, H-12a), 1.66 (1H, m, H-12b), 4.24 (1H, d,
J=2.8Hz, H-14), 4.90 (1H, s, H-16a), 4.86 (1H, s, H-16b), 1.75 (3H, s, H-17), 1.30 (3H, s, H-
18), 1.79 (3H, s, H-19), 3.94 (1H, d, J=12.0Hz, H-20a), 3.75 (1H, d, J=12.0Hz, H-20a),
1.81(2H,m,H-2′),1.56(2H,m,H-3′),1.29(1H,m,H-4′a),1.72(1H,m,H-4′b),1.17(1H,m,
H-5′a),1.56(1H,m,H-5′b),1.10(1H,m,H-6′a),1.56(1H,m,H-6′b),1.25(1H,m,H-7′a),
1.46(1H,m,H-7′b),2.32(1H,m,H-8′a),1.10(1H,m,H-8′b),2.09(1H,m,H-9′),1.04(3H,d,
J=7.1Hz, H-10 ').13C-NMR(150MHz,CDCl3),δC:54.1(C-1),112.9(C-2),173.3(C-3),86.6
(C-4),67.7(C-5),60.0(C-6),59.4(C-7),35.9(C-8),81.1(C-9),48.9(C-10),37.4(C-
11),37.0(C-12),84.0(C-13),81.3(C-14),146.3(C-15),111.4(C-16),18.7(C-17),21.3
(C-18),20.1(C-19),63.9(C-20),119.5(C-1′),33.8(C-2′),20.4(C-3′),28.9(C-4′),
26.0(C-5′),24.4(C-6′),24.6(C-7′),25.5(C-8′),29.5(C-9′),18.9(C-10′).
Embodiment 3
The most first prepare compound pimelotide C, after dissolving with a small amount of DMSO, fill routinely
Penetrating and use water, fine straining, injection is made in embedding sterilizing.
Embodiment 4
The most first prepare compound pimelotide C, after dissolving with a small amount of DMSO, be dissolved in nothing
In bacterium water for injection, it is stirred to dissolve, filters with aseptic suction funnel, more aseptic fine straining, it is sub-packed in ampoule, low temperature cold lyophilizing
After dry, aseptic sealing by fusing obtains injectable powder.
Embodiment 5
By the compound pimelotide C of 1 isolated of embodiment, press it respectively with excipient weight ratio for 9:1's
Ratio adds excipient, makes powder.
Embodiment 6
The most first prepare compound pimelotide C, press it respectively with excipient weight ratio for 5:1's
Ratio adds excipient, pelletizing press sheet.
Embodiment 7
The most first preparing compound pimelotide C, oral liquid preparation method is made oral the most routinely
Liquid.
Embodiment 8
The most first prepare compound pimelotide C, in its with excipient weight than the ratio for 5:1
Add excipient, make capsule.
Embodiment 9
The most first prepare compound pimelotide C, in its with excipient weight than the ratio for 3:1
Add excipient, make capsule.
Embodiment 10
The most first prepare compound pimelotide C, press it respectively with excipient weight ratio for 5:1's
Ratio adds excipient, makes granule.
Claims (5)
1. daphane diterpene compound pimelotide C application in preparing anti-hepatitis B medicine.
2. the pharmaceutical composition of an anti-hepatitis B virus, it is characterised in that containing daphane diterpene compound
pimelotideC。
3. the pharmaceutical composition of an anti-hepatitis B virus, it is characterised in that the daphane diterpene chemical combination containing 0.1-99%
Thing pimelotide C, remaining is pharmaceutically acceptable carrier and/or excipient.
The pharmaceutical composition of a kind of anti-hepatitis B virus the most as claimed in claim 3, it is characterised in that containing 0.5-90%
Daphane diterpene compound pimelotide C.
5. the preparation method of a daphane diterpene compound pimelotide C, it is characterised in that comprise the steps: to take
Flos wikstroemiae chamaedaphnes (Flos et follium wikstroemiae chamaedaphnis), with 95% alcohol reflux twice, each 3 hours, merges ethanol extract, and recovered under reduced pressure is to without alcohol, by addition phase
The distilled water of same volume dissolves, and then extracts by ethyl acetate, and extract concentrate drying becomes extractum, extractum 80% ethanol
Dissolving is adsorbed on silica gel, and room temperature is placed and volatilized solvent, grinds after sieving through silica gel column chromatography, with volume ratio 7:3,5:5,3:7
Petroleum ether-ethyl acetate gradient elution, obtain 3 components A-C, component C is suppressed standby in ODS C-18gel post, uses body
The long-pending methanol-water gradient elution than 5:95 to 95:5, obtains 5 stream part C1～C5；C4, through Sephadex gel filtration chromatography, uses body
Long-pending ratio 1:1 chloroform-methanol eluting, obtains 6 flow point C4-1～C4-6；Flow point C4-3 is prepared through HPLC, by volume ratio 75:25 second
Nitrile-water elution, purification obtains compound pimelotide C.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556346A (en) * | 2017-10-18 | 2018-01-09 | 山西大学 | A kind of anti-hepatitis B virus Lathyrane type diterpene-kind compounds and its preparation method and application |
| CN110538243A (en) * | 2018-05-29 | 2019-12-06 | 复旦大学 | Preparation method of active total diterpene in Thymelaeaceae plant and application thereof in pharmacy |
| CN111138399A (en) * | 2020-01-09 | 2020-05-12 | 山西大学 | Total flavone extract with antioxidant effect, and preparation method and application thereof |
| CN114031579A (en) * | 2021-11-11 | 2022-02-11 | 沈阳药科大学 | Preparation and application of daphnane diterpenoid compounds in lilac daphne flower buds |
| CN116854704A (en) * | 2023-07-06 | 2023-10-10 | 沈阳药科大学 | Daphnane diterpenoid derivative with anti-liver cancer activity and preparation method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556346A (en) * | 2017-10-18 | 2018-01-09 | 山西大学 | A kind of anti-hepatitis B virus Lathyrane type diterpene-kind compounds and its preparation method and application |
| CN107556346B (en) * | 2017-10-18 | 2020-04-17 | 山西大学 | Anti-hepatitis B virus Lathyrane diterpenoid compound and preparation method and application thereof |
| CN110538243A (en) * | 2018-05-29 | 2019-12-06 | 复旦大学 | Preparation method of active total diterpene in Thymelaeaceae plant and application thereof in pharmacy |
| CN111138399A (en) * | 2020-01-09 | 2020-05-12 | 山西大学 | Total flavone extract with antioxidant effect, and preparation method and application thereof |
| CN114031579A (en) * | 2021-11-11 | 2022-02-11 | 沈阳药科大学 | Preparation and application of daphnane diterpenoid compounds in lilac daphne flower buds |
| CN114031579B (en) * | 2021-11-11 | 2023-03-07 | 沈阳药科大学 | Preparation and application of daphnane diterpenoid compounds in lilac daphne flower buds |
| CN116854704A (en) * | 2023-07-06 | 2023-10-10 | 沈阳药科大学 | Daphnane diterpenoid derivative with anti-liver cancer activity and preparation method and application thereof |
| CN116854704B (en) * | 2023-07-06 | 2024-05-07 | 沈阳药科大学 | Daphnane diterpenoid derivative with anti-liver cancer activity and preparation method and application thereof |
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| Publication number | Publication date |
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| CN106176716B (en) | 2018-10-19 |
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